A group of immigration activists speak out against raids on undocumented immigrants, during a rally in front of the White House in Washington January 8, 2016. Jonathan Ernst / Reuters

A lifetime ago, some legal thinkers bristled at the supposed “executive overreach” of Barack Obama’s immigration policy. That policy was spelled out in a series of carefully written guidance memos—issued in regular order by the Secretary of Homeland Security rather than the president, and prepared after careful review by the Office of Legal Counsel.

What will executive power specialists make of President Donald Trump’s recent executive order announcing a crackdown on “sanctuary jurisdictions”—meaning cities, counties, and state agencies that stay aloof from federal immigration enforcement? The document, not to put too fine a point on it, reads as if The Simpsons’ Lionel Hutz sat up all night cutting words out of a magazine and pasting them on a brown paper bag. (In fact, National Public Radio reported that the Office of Legal Counsel, which is supposed to review all federal orders, refused to say whether it had even seen the “sanctuary” order.)

Trump’s order, among other things, seeks to force state and local authorities to actively enforce federal statutes. The conservative legal movement has given that part of the order’s foes some powerful legal weapons. A 1997 case, Printz v. United States, says that the federal government may never order local officials to enforce federal law; the famous 2012 Affordable Care Act case, National Federation of Independent Business v. Sebelius, says that the government cannot use the threat of large funding cuts to “coerce” states into adopting federally demanded policies. The order seems to implicate both constitutional rules.

On the “coercion” issue, the order in fact is best read as a threat—political and financial––against any local government that does not follow any federal orders in the immigration context. It denounces some unnamed local leaders in non-legal language: “Sanctuary jurisdictions across the United States willfully violate Federal law in an attempt to shield aliens from removal from the United States. These jurisdictions have caused immeasurable harm to the American people and to the very fabric of our Republic.”

Of course, many people dislike “sanctuary jurisdictions” without knowing exactly what they are. That’s because there is no real definition. The closest thing to one in the order is this:

jurisdictions that willfully refuse to comply with 8 U.S.C. 1373 (sanctuary jurisdictions) are not eligible to receive Federal grants, except as deemed necessary for law enforcement purposes by the Attorney General or the Secretary [of Homeland Security]. The Secretary has the authority to designate, in his discretion and to the extent consistent with law, a jurisdiction as a sanctuary jurisdiction.

The statute it cites, part of the Illegal Immigration Reform and Immigrant Responsibility Act of 1996, provides that “a Federal, State, or local government entity or official may not prohibit, or in any way restrict, any government entity or official from sending to, or receiving from, [federal immigration officers] information regarding the citizenship or immigration status, lawful or unlawful, of any individual” or “maintaining” or “exchanging” such information with other federal and state law enforcement agencies.

This is a kind of linguistic wormhole—state and local “entities and officials” can’t give instructions to other state and local “entities and officials” limiting the information. Thus, by its terms, a city council cannot adopt an ordinance forbidding the police from notifying U.S. Immigration and Customs Enforcement that they have arrested an alien who may be undocumented. A number of cities have rules against such notifications; but the order sweeps in much more. By its terms, Chief Daniels can’t tell Officers Bunk and McNulty not to notify ICE even in a particular case (say of an undocumented alien who is also a key witness in an ongoing investigation). Bunk and McNulty can’t tell the booking sergeant not to do it even if they want the witness to stick around. The booking sergeant can’t even tell the janitor not to do it.

All authority over this one kind of communication has been transferred from state officials to the individual employee, free of state control.

This brings us to Printz. Under the Brady Handgun Violence Prevention Act of 1993, all purchasers of hand weapons are supposed to receive a background check before buying a gun. However, when the bill took effect, the planned federal database for gun dealers (which was supposed to reveal criminal records or mental illness, etc.) was not ready; so the bill temporarily assigned the duty of conducting a check to the “chief law enforcement officer” of each city or county, who was required to send the information produced to the federal government. That meant that two rural Western sheriffs, Jay Printz and Richard Mack, were required by federal law to spend time and effort digging out the criminal and other records of prospective gun owners and reporting them to Washington.

They cried foul, and the Supreme Court agreed, holding that “the Federal Government may not compel the States to enact or administer a federal regulatory program.” That meant that federal statutory commands to state law officers—“you will hold the following people in jail,” for example--are void. This rule—that the federal government can’t order states to pass laws or require state officials to enforce federal laws—is known as the “anti-commandeering principle.”

The weird language of 1373 seems to have been an attempt to avoid a “commandeering” problem. It doesn’t say that the state entities must provide information; it says that they can’t prevent themselves from providing it--“you may not refuse to voluntarily obey.” It is akin to the “bewilderingly psychological” commands of the hypnotist in Thomas Mann’s Mario and the Magician, who overcomes resistance by telling his victims that though they may not want to obey him, they can’t actually wish not to obey him either.

The Court has repeatedly stressed the need for state autonomy in the area of local law enforcement; thus the statute seems like a bad overreach. A federal court in 1998 upheld 1373 against a challenge by New York and its (then) pro-immigrant mayor, Rudolph Giuliani. But the language of that case is carefully limited—the Second Circuit left open the possibility that a city or state could enforce a law forbidding law enforcement from revealing immigration status to anyone, but not one barring only telling the federal government.

In addition, even that limit in the decision seems wrong. In an interview yesterday, Ohio State University Professor Peter Shane, who has studied both federalism and presidential authority, phrased it this way: “There is nothing to the idea of state sovereignty if state and city officials are not entitled to direct how their subordinates exercise their lawful discretion to advance state and local interests.”

The order’s second problem is that, though 1373 is the only statute it mentions, it seeks to punish conduct not covered by the statute. There’s no standard set of “sanctuary” policies, but over the years ICE has objected to a number of provisions adopted by cities and counties. In some, local law enforcement officers are forbidden to ask those they interview—suspects, victims, or witnesses—about their immigration status. (That is not, by the way, purely to cock a snook at ICE; many police chiefs believe that witnesses and victims will stop reporting crimes if they fear being turned over to ICE.) Thus, there would be no immigration information to transmit. 1373 doesn’t order—and couldn’t order––local police to ask immigration questions. But the order vaguely threatens those who don’t.

In other jurisdictions, local jails refuse to comply with “ICE detainers.” Given the new plans to detain many more undocumented people, the “detainer” issue is a crucial one. When an alien is arrested by local police, the feds want the police to notify ICE, so it can check the alien’s immigration status. If the alien seems like a person ICE even might want to deport, it can issue a “detainer” to the local jail. Under the “detainer,” the jail is supposed to hold the alien (at state expense) for 48 hours. Even if the charges for which the alien has been arrested are dropped, ICE asks the locals to keep the alien under lock and key until they can come get him or her.

And that’s a problem: under the U.S. Constitution, police are not allowed to keep people in jail unless there is a warrant from a court, or probable cause to believe they have committed a crime. An administrative order (“we kinda think we might have a reason to talk to this person”) isn’t probable cause, and ICE isn’t a court.

Four federal courts—in Pennsylvania, Rhode Island, Oregon. and Illinois—have held that holding prisoners on ICE detainers violates the Fourth Amendment. (In two of those cases, by the way, the “suspect” aliens turned out to be U.S. citizens.) The court in Illinois also held that ICE doesn’t even have the authority under its own statute to issue the detainers.

Two of these courts also held that counties who illegally hold aliens cannot use the federal “detainer” as a defense against lawsuits. Remember, federal officials cannot issue direct orders to state officials; so, the judges reasoned, the locals were voluntarily choosing to violate the Constitution. In other words, local taxpayers not only pay the cost of jailing the suspects; they will pay the damages when those illegally detained bring a lawsuit.

The executive order actually does not order “sanctuary jurisdictions” to collect or provide information, and it does not even mention ICE detainers. Instead, it vaguely mentions 1373 and then says, in essence, “Nice local government you got here—shame if anything bad happened to it.”

Under last week’s order, the Secretary of Homeland security “has the authority to designate, in his discretion and to the extent consistent with law, a jurisdiction as a sanctuary jurisdiction.” After that, the Attorney General shall take “appropriate enforcement action” against “any entity that violates 8 U.S.C. 1373, or which has in effect a statute, policy, or practice that prevents or hinders the enforcement of Federal law.” That phrase isn’t tied to any statute, and could mean anything from firing on Fort Sumter to not returning ICE phone calls until after lunch. Enforcement apparently means an order that the “guilty” jurisdiction shall not be “eligible to receive Federal grants, except as deemed necessary for law enforcement purposes.”

Read carefully, that seems to mean that any jurisdiction that displeases ICE—whether by ignoring 1373 or for any other reason—may be stripped of a wide variety of federal funding. Let’s walk it through: a barely comprehensible executive order, citing no statute, permits a federal official to affix a meaningless label on any local government or agency—and then permits another federal official, at his or her sole discretion, to impose a financial penalty of unspecified size against almost any sources of federal funds.

That brings us to the Sebelius case. As originally passed, the Affordable Care Act instructed states with Medicaid programs (that is, all states) to change the programs’ criteria to cover more people. Again, such a bald order would be unconstitutional. But Medicaid is largely funded by the federal government, and federal funding programs can require states to agree in advance to certain conditions in exchange for the funds. The Medicaid statute warned states that Congress could change the conditions at any time. So the ACA provided massive increases in Medicaid funding to each state––and required the state accepting the funds, in return, to expand the Medicaid program.

Florida challenged the requirement, and the Supreme Court supported the state, 7-2. An opinion written by Chief Justice Roberts and joined by Justices Stephen Breyer and Elena Kagan, held for the first time that the federal government can’t change the conditions for grant programs if “such conditions take the form of threats to terminate other significant independent grants,” or “penalize States that choose not to participate in that new program by taking away their existing ... funding.” The federal government had to continue funding state Medicaid programs—even if they didn’t expand.

The precise outlines of this new limit aren’t clear—but on its face, Wednesday’s executive order seems to defy any limit at all.

All this means that brilliant liberal lawyers representing blue states, cities, and public schools and colleges will soon be quoting arguments pioneered by brilliant conservative lawyers representing red states and lawmen over the past 20 years. The executive order, as I said, is only partly concerned with states and “sanctuary jurisdictions”; but that part is sending a coded message: SUE ME.

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